Automate or Die Trying

Wil Ramos
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A show exploring how today’s tech leaders secure innovation through automation and trust. Hosted by Wil Ramos, each episode shares real stories and lessons in DevSecOps, AI security, and building resilient modern organizations.

  1. 12/04/2025

    “How Brian Shea Went from Defense to Disrupting the AI Industry”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Brian Shea, a security executive, published author, and trusted leader in security, compliance, and technology. Brian shares his journey from military service to leading technology and security teams at Fortune 50 companies like Bank of America, Microsoft, and Salesforce, and now helping professionals pivot into new career opportunities through AI and “vibe coding.” The conversation dives into the balance between speed and security in technology, the challenges of AI-assisted coding, and the importance of prompt specificity. Brian reflects on his career path, emphasizing transferable skills, adaptability, and the value of disciplined experimentation. He also explores trust in engineering teams, proactive vs. reactive security, and the role of humans in AI-assisted decision-making. Finally, Brian discusses his AI startup, inspired by helping his wife’s Pilates business, and shares practical advice for leaders seeking to move fast without breaking things, highlighting ethical and thoughtful approaches to AI implementation. Key Takeaways: Why balancing speed and security is critical in tech at scaleHow AI can accelerate coding while requiring disciplined engineering practicesThe importance of prompt specificity to guide AI output effectivelyLessons from a non-linear career: leveraging transferable skills and curiosityBuilding trust in engineering teams through guardrails, monitoring, and transparencyBalancing proactive and reactive security strategies in high-stakes environmentsWhy humans remain essential in AI-assisted decision-makingPractical advice for moving fast without breaking systems: plan first, act secondThe inspiration and vision behind Brian’s AI startup to support career pivots Golden Nugget: “AI can do amazing things, but humans are still the final line of defense. Plan carefully, act thoughtfully, and use technology to amplify, not replace, our judgment.” Connect with Brian Shea: LinkedIn: linkedin.com/in/brianshea Listen Now & Subscribe: Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    33 min

  2. 12/04/2025

    “How Meade Kincke Became the Recalibrator for Elite Veterans & High-Performance Leaders”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Meade Kincke, better known as The Recalibrator, a keynote speaker, transformation coach, and trusted advisor to elite veterans, former agency professionals, founders, and Fortune 500 executives from companies like AT&T, eBay, and Yum! Brands. Meade shares his unconventional journey from hacking in basements to becoming a strategic coach for some of the most disciplined minds in the world. For more than two decades, he has helped special operations veterans transition into meaningful civilian careers, guided executives through high-stakes leadership challenges, and supported entrepreneurs seeking clarity, purpose, and performance at scale. The conversation dives deep into identity, reinvention, and the psychological reset required to shift from one intense chapter of life to the next. Meade breaks down the emotional realities veterans face when leaving service, describing it as a strange kind of death, and explains how he helps them rebuild purpose, confidence, and direction. He also unpacks his philosophy on simplicity in engineering and leadership, arguing that the most resilient systems and the most resilient people are the ones built on boredom, consistency, and disciplined fundamentals. Flashy tools do not build trust; predictable systems do. Meade discusses the importance of environment when working with top performers, explaining why he uses his Pint Test to evaluate whether people should actually work together. Talent matters, but trust, compatibility, and emotional safety matter more. When those elements align, teams move faster, make smarter decisions, and prevent burnout before it starts. The episode also explores veterans in tech, how companies can better support high-pressure transitions, and why automation, compliance, and security often fail when leaders assume the work is set and forget. Meade emphasizes that real security, whether technical or personal, requires relentless recalibration, not checkboxes. Finally, Meade shares practical advice for executives, veterans, and founders who are looking to make major shifts in their lives. Whether navigating identity loss, career pivots, or overwhelming leadership responsibility, Meade’s framework helps people slow down, reassess, and rebuild from a place of clarity and strength. Key Takeaways:Why elite veterans struggle with identity loss after service and how recalibration restores purposeHow disciplined curiosity and boring consistency build stronger engineering and leadership systemsWhy simplicity is more secure than complexity, especially in high-stakes environmentsHow the Pint Test helps leaders build trust-based, high-performance teamsWhy more companies are hiring fewer people and paying them more to get better resultsThe difference between compliance checkboxes and real securityWhy major life transitions require psychological decomposition before reconstructionPractical steps for leaders, veterans, and founders seeking clarity, confidence, and direction Golden Nugget: “Recalibration is not about starting over. It is about stripping away what no longer serves you so you can rebuild with purpose, discipline, and clarity.” Connect with Meade Kincke: LinkedIn: linkedin.com/in/meadekincke Website: https://therecalibrator.com/ Substack: https://meadekincke.substack.com/ YouTube: a href="https://www.youtube.com/@meadekincke"...

    32 min

  3. 12/15/2025

    “How Bob Fabien “BZ” Zinga Went from Navy Cyber Warfare to Turning Security into a Growth Engine”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Bob Fabien “BZ” Zinga, a trusted cybersecurity executive, servant leader, boardroom strategist, and Navy Commander whose career spans defending global military networks and enabling hypergrowth inside AI and SaaS companies. Ranked in the Top 3% of LinkedIn worldwide and the #1 U.S. content creator for #GlobalLeaders and #RiskandResilience, BZ brings a rare blend of military discipline, startup speed, and human-centered leadership. BZ shares his journey from commanding Navy cyber operations and safeguarding mission-critical global systems to adapting his leadership style for engineering-driven Silicon Valley environments. He opens up about the culture shock of transitioning from authority-based leadership to influence-based leadership and explains why security only matters when it enhances speed, predictability, and trust. The conversation dives deep into how BZ built security programs that empower developers rather than block them, embedding guardrails directly into engineering workflows to support rapid innovation. He breaks down how he helped an AI automation startup scale 50x in revenue, shorten sales cycles by 39 days, and use security as a competitive advantage to win enterprise customers. Finally, BZ reflects on the personal evolution required to lead across radically different cultures, balancing mission assurance, business outcomes, relationship-building, and resilience. He shares why the safest path must also be the fastest path and how security becomes a true multiplier for growth when leaders focus on clarity, collaboration, and customer trust. Key Takeaways: Why modern security must function as a velocity engine, not a barrierHow to lead engineering teams through influence, empathy, and credibilityThe power of embedding security guardrails into high-speed development workflowsHow security can accelerate sales cycles and drive enterprise revenueA practical framework for risk modeling based on impact, velocity, and blast radiusWhy relationship-building is a core competency for security leadersHow evidence automation and trust signaling create measurable business valueLessons from leading at global military scale and in high-growth startupsWhy “the safest path must be the fastest path” for responsible innovation Golden Nugget: “Security should give your organization the confidence to move faster, not slow it down. When you build the right guardrails, you unlock velocity, trust, and sustainable innovation.” Connect with Bob Fabien “BZ” Zinga: LinkedIn: linkedin.com/in/bobfabienzingaWebsite: bobfabienzinga.com Linktree: linktr.ee/bobfabienzinga Creator Spotlight: spotlight.favikon.com/bobfabienzinga/ Listen Now & Subscribe: Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    32 min

  4. 12/16/2025

    “How Sunil Sharma Went from AI and XR Innovation to Transforming Trauma Care”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Sunil Sharma, CTO and CEO at a stealth-mode AI MedTech startup focused on XR and data science. Sunil shares his journey from leading data science and platform engineering at companies like Thermo Fisher Scientific and ADP to building systems that scale, innovate, and save lives. The conversation dives into how his team is transforming the “golden hour” into “golden minutes” for trauma victims, enabling first responders, even non-medical personnel to triage patients effectively in high-stakes environments. Sunil discusses predictive models, XR-enabled glasses that monitor vitals remotely, and hybrid AI systems designed for safety, speed, and accuracy. He also reflects on lessons learned scaling enterprise systems, implementing agile transformations, and building high-quality, actionable AI data pipelines. Finally, Sunil shares practical advice for leaders developing AI-driven medical solutions, emphasizing collaboration, context-aware AI, and rigorous testing to ensure life-saving impact. Key Takeaways: How AI and XR compress the “golden hour” in trauma careDesigning AI systems for high-stakes environments with robust fail-safesScaling enterprise-grade systems for speed, precision, and reliabilityEnsuring data quality and context-awareness in hybrid AI modelsLessons from leading innovation labs and accelerating product development cyclesThe role of humans in AI-assisted decision-making and emergency triage Golden Nugget: “Technology can save lives, but it works best when humans remain in the loop. The right AI, in the right hands, can turn minutes into miracles.” Connect with Sunil Sharma: LinkedIn: linkedin.com/in/sunil-sharma-leader Listen Now & Subscribe: Apple Podcasts, Spotify,  Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    43 min

  5. JAN 5

    “How Todd Merrill Went from Cable Modems to Scaling AI Without Breaking Security”

    Episode Summary:In this episode of Automate or Die Trying, host Wil Ramos sits down with Todd Merrill, Partner and Fractional CTO at TechCXO, Global Top 25 Consultant, and AI investor with more than 30 years of experience building mission-critical systems. Todd shares his journey from holding patents on the first cable modem and deploying software on space-shuttle-launched satellites, to running early AWS production workloads, and now advising startups and enterprises on scaling AI securely. He explains how his background in telecom, cybersecurity, and embedded systems shaped his disciplined approach to reliability and risk. The conversation explores AI and automation at scale, including why Todd was initially skeptical of large language models and what changed his perspective. He discusses how tool-augmented AI, connected to real enterprise systems, is unlocking hyper-productivity—while also introducing new security and operational challenges. Finally, Todd shares practical advice for leaders adopting AI, emphasizing human-in-the-loop systems, strong change management, and protecting customer data as non-negotiables when moving fast Key Takeaways:How AI has changed the economics of building and scaling softwareWhy security gets harder as systems become more complexThe role of human-in-the-loop AI in high-stakes environmentsCommon security shortcuts that put fast-growing companies at riskWhy change management—not technology—derails most transformations Golden Nugget:“AI won’t replace people, but it will make capable people dramatically more powerful when security and judgment come first.” Connect with Todd Merrill:LinkedIn: linkedin.com/in/toddmerrillCompany: techcxo.com/partners/todd-merrill/ Listen Now & Subscribe: Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    26 min

  6. JAN 6

    “How Mex Emini Went from Scaling iGaming Data Engines to Redefining Decision Intelligence”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Mex Emini, Co-Founder of DataFlair.ai and former CTO of Sigma, the world’s largest iGaming festival network. Mex shares how his 16 years in data-driven industries have shaped his belief that insights alone aren’t enough; what matters is what happens after the data. The conversation explores why most companies stall at dashboards, how broken processes undermine automation, and why decision intelligence must be contextual, outcome-focused, and action-oriented. Mex breaks down how DataFlair.ai turns fragmented data into trusted recommendations, helping businesses move faster, pivot earlier, and make smarter decisions at scale. Mex also reflects on scaling global teams, deciding when humans stay in the loop, and how AI should amplify talent rather than replace it. He closes with practical guidance for leaders navigating automation, AI adoption, and high-stakes decision-making. Key Takeaways: Why dashboards fail to drive real business actionThe difference between output and outcome in automationHow contextualized AI recommendations build trustWhen to automate and when humans must stay involvedScaling decision intelligence without automating broken processes Golden Nugget: “You can’t automate a broken process. Measure what matters, focus on outcomes, and let AI amplify human judgment.” Connect with Mex Emini: Mex’s Profile linkedin.com/in/mexiterWebsite about.dataflair.aI Listen Now & Subscribe: Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    16 min

  7. JAN 12

    “How Sara Fuerst Went from CTO to CEO While Automating Security and Scaling BeHerVillage”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Sara Fuerst, CTO and Co-Founder of BeHerVillage, founder of TIBSar Software, and a technical leader navigating the transition from CTO to CEO while scaling a mission-driven startup. Sara shares her journey building BeHerVillage, a baby registry focused on supporting moms rather than just babies, and growing it to nearly $500,000 in gifted funds. She explains how her diverse technical and entrepreneurial background shaped her approach to automation, efficiency, and security. The conversation explores how Sara leverages AI and automation across content workflows, social media, and technical monitoring, while ensuring the human element remains central. She discusses implementing secure systems, handling cyber threats, integrating third-party services like Cloudflare and DigitalOcean, and the lessons she’s learned prioritizing what to automate in a resource-constrained startup. Finally, Sara shares her philosophy on AI, balancing human customer service with intelligent automation, and her vision for guiding first-time parents through personalized support and education using technology. Key Takeaways: How Sara uses automation to reclaim time and scale operationsPrioritizing automation based on value and human oversightApproaches to secure AI implementation in small, growing startupsMaintaining human-centered customer service even as AI adoption growsLessons learned transitioning from CTO to CEO while building a mission-driven businessAvoiding automation pitfalls, like runaway email loopsLeveraging AI for content creation, brainstorming, and parent guidance Golden Nugget: “Perfection is the enemy of progress. Focus on solving your customers’ problems first, automate what frees you to lead, and never let AI replace genuine human connection.” Connect with Sara Fuerst: LinkedIn: linkedin.com/in/sarafuerstCompany Website: tibsarsoftware.comBeHerVillage Instagram: @BeHerVillageBeHerVillage Website: behervillage.comBirth Worker Partner Listing: a href="https://behervillage.com/partners" rel="noopener noreferrer"...

    27 min

  8. JAN 14

    “How Dr. Glen Vickers Went from Help Desk to Rebuilding Mission-Critical Systems Without Breaking Uptime”

    Episode Summary: In this episode of Automate or Die Trying, host Wil Ramos sits down with Dr. Glen Vickers, a technology and cybersecurity leader with global impact across cloud, SaaS, DevOps, and enterprise security. Dr. Vickers shares his decades-long journey from early help desk roles to leading complex, mission-critical technology environments under extreme operational constraints. Dr. Vickers explains how hands-on experience across infrastructure, cybersecurity, and enterprise platforms shaped his disciplined approach to reliability, governance, and secure-by-design systems. He discusses rebuilding fragmented technology organizations, stabilizing legacy platforms, and delivering measurable improvements in uptime, security posture, and operational efficiency. The conversation explores cybersecurity and AI in production environments, emphasizing identity-first security, data classification, and the importance of human judgment in high-stakes systems. Dr. Vickers outlines why integrity, governance, and people-first leadership are essential when scaling technology responsibly. Finally, he shares practical advice for technology leaders navigating modernization, AI adoption, and cybersecurity risk—without sacrificing trust, resilience, or business continuity. Key Takeaways: How to rebuild and stabilize mission-critical systems without downtimeWhy identity and data governance are foundational to cybersecurity and AIBalancing modernization with legacy system realitiesThe role of human judgment in secure, AI-enabled environmentsWhy secure-by-design thinking must start at the leadership level Golden Nugget: “Security isn’t something you add later. If systems and teams aren’t built with integrity from the start, speed will eventually work against you.” Connect with Dr. Glen Vickers: LinkedIn: linkedin.com/in/drglenvickers Listen Now & Subscribe: Apple Podcasts, Spotify, Amazon Music, or find us wherever you get your podcasts. Powered by cybersecurityprivacy.com Automate or Die Trying empowers leaders to adopt AI securely, move faster with confidence, and transform the future of work.

    30 min
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About

A show exploring how today’s tech leaders secure innovation through automation and trust. Hosted by Wil Ramos, each episode shares real stories and lessons in DevSecOps, AI security, and building resilient modern organizations.

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  • Creator
    Wil Ramos
  • Years Active
    2K
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Wil Ramos
  • Show Website
    Automate or Die Trying